Categories: Synthesis of N-Heterocycles >
Synthesis of oxindoles
Recent Literature
A highly regioselective palladium-catalyzed cyclization converts
α-chloroacetanilides to oxindoles in good to excellent yields with high
functional group compatibility using 2-(di-tert-butylphosphino)biphenyl
as ligand and triethylamine as a stoichiometric base.
E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc.,
2003, 125, 12084-12085.
Chiral N-heterocyclic carbene (NHC) ligands having a 2,2′-bisquinoline-based
C2 symmetric skeleton exhibited good enantioselectivity in
palladium-catalyzed intramolecular α-arylation of amides to give
3,3-disubsituted oxindoles.
L. Liu, N. Ishida, S. Ashida, M. Murakami, Org. Lett., 2011,
13, 1666-1669.
A palladium catalyst derived from an air-stable secondary phosphine oxide
enabled efficient intramolecular α-arylations of amides with aryl chlorides to
give various substituted oxindoles and azaoxindoles in good yield.
L. Ackermann, R. Vicente, N. Hofmann, Org. Lett., 2009,
11, 4274-4276.
Highly efficient conditions for the preparation of 3,3-disubstituted oxindoles
by a formal C-H, Ar-H coupling of anilides have been identified using catalytic
Cu(OAc)2•H2O with atmospheric oxygen as the reoxidant in
mesitylene or toluene as solvent; no additional base is required.
J. E. M. N. Klein, A. Perry, D. S. Pugh, R. J. K. Taylor, Org. Lett., 2010,
12, 3446-3449.
A small library of α,β-unsaturated oxindoles was prepared by an efficient
microwave-assisted one-pot sequence comprising an aromatic substitution
followed by an ionic Horner-Wadsworth-Emmons olefination.
A. Teichert, K. Jantos, K. Harms, A. Studer, Org. Lett., 2004, 6, 3477-3480.
